Hydrochloric Acid → Pyridine, 2,3,5-trichloro-

HRID 1284434Notes

Reaction equation

HRID 1284434 reaction equation
N[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.N([O-])=O.[Na+].CCOCC.CCCCCC.[ClH:25]>O>[Cl:25][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 778863,5-Dichloro-3-pyridylamineHCID 21584099Diethylether hexaneHCID 23668193Sodium Nitrite

Product 1

HCID 27666Pyridine, 2,3,5-trichloro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-3,5-dichloropyridine (21.0 g.) is dissolved in conc. HCl (200 ml.), then cooled with ice. To this solution, NaNO2 (48 g.) in water (60 ml.) is added slowly over 30 minutes. The reaction mixture is stirred at 0° for 1 hour and then 50° for 1 hour. The mixture is then poured into ice-water and extracted with ether. The combined extracts are washed, dried and evaporated to dryness to give yellow solid. The solid is stirred with 25% ether/hexane and filtered. The filtrate is concentrated and washed again with 25% ether/hexane to give 2,3,5-trichloropyridine (12 g.).

Workup

  1. temperaturecooled with ice
  2. wait50° for 1 hour
  3. extractionextracted with ether
  4. washThe combined extracts are washed
  5. customdried
  6. customevaporated to dryness
  7. customto give yellow solid
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated
  10. washwashed again with 25% ether/hexane

Sources & evidence

ORD record
ord-f5e3544494074d1b8daf13e34fd1f83c
Source dataset
uspto-grants-1986_01
Patent number
US04563310

Reaction notes

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